Playboy Playmate Pajama Party 1999 A departure from the traditional Playboy video fare Title is shot entirely on the grounds of the Playboy Mansion, and includes some historic footage regarding the events that took place there The Playmates explore the grounds, including swimming in and sunning themselves beside the Grotto roaming au naturel through Hefs private menagerie playing a clothing challenged game of tennis relaxing with a full body massage and a hot shower playing an impromptu game of strip poker shooting pool, and celebrating good shots by disrobing taking a nighttime dip in the Grotto and engaging in a pillow fight, where the first casualties are their tiny outfits Title switches between filmed segments and sequences shot on video believed to be a first for Playboy